Affiliation:
1. Research Institute for Medicines (iMed.ULisboa) Faculty of Pharmacy Universidade de Lisboa Av. Prof. Gama Pinto 1649-003 Lisbon Portugal
2. Faculty of Engineering and Natural Sciences Tampere University Korkeakoulunkatu 8 33101 Tampere Finland
Abstract
Abstract(−)‐Agelastatin A was synthetized employing a flow photorearrangement of a pyridinium salt, constructing in one step the cyclopentene core possessing the desired functionalities and relative configurations. A flow enzymatic kinetic resolution of the resulting bicyclic vinyl aziridine delivered the enantiopure precursor to the natural product. This total synthesis required the use of a single protective group. Two novel agelastatin N3‐derivatives were synthesized and their cytotoxicity evaluated against a series of cancer cell lines, which corroborated the importance of unsubstituted N3 in the biological activity of (−)‐agelastatin A.
Cited by
2 articles.
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